Br[C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].C(=O)([O-])[O-].[K+].[K+].[S:18]1[CH:22]=[CH:21][C:20](B(O)O)=[CH:19]1>O1CCOCC1.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[S:18]1[CH:22]=[CH:21][C:20]([C:2]2[CH:3]=[C:4]([CH:9]=[CH:10][CH:11]=2)[C:5]([O:7][CH3:8])=[O:6])=[CH:19]1Nitrogen (gas) was bubbled through the solution of methyl 3-bromobenzoate (50 mg, 0.233 mmol), potassium carbonate (96 mg, 0.698 mmol) and 3-thiopheneboronic acid (59.5 mg, 0.465 mmol) in dioxane (2 mL) and Water (0.2 mL) for 5 minutes. tetrakis(triphenylphosphine)palladium(0) (26.9 mg, 0.023 mmol) was added and again nitrogen was bubbled through the solution for 5 minutes. The reaction mixture was heated overnight at 100° C. and concentrated to dryness. Purified by chromatography (20% EtOAc in heptane) gave compound methyl 3-(thiophen-3-yl)benzoate 82 (50 mg, 99%). (m/z)=219 (M+H)+.
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